Chloroacetic anhydride Chemical Properties

Melting point:

51 °C

Boiling point:

203 °C

Density 

1.449

vapor pressure 

<0.75 mm Hg ( 20 °C)

refractive index 

1.4730 (estimate)

Flash point:

>230 °F

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

Freely soluble in ether, chloroform. Slightly soluble in benzene. Insoluble in cold ligroin

form 

Crystals, Chunks or Low Melting Mass

color 

brown

Sensitive 

Moisture Sensitive

Merck 

14,2113

BRN 

774533

Stability:

Moisture Sensitive

InChIKey

PNVPNXKRAUBJGW-UHFFFAOYSA-N

CAS DataBase Reference

541-88-8(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, chloro-, anhydride (541-88-8)

Safety Information

Hazard Codes 

C,T

Risk Statements 

34-36/37-43-25

Safety Statements 

26-28-36/37/39-45-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-19-21

Hazard Note 

Highly Toxic/Corrosive/Lachrymator

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29159000

Hazardous Substances Data

541-88-8(Hazardous Substances Data)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Chloroacetic anhydride Usage And Synthesis

Chemical Properties

brownish semi-transparent crystals, chunks or low

Uses

Chloroacetic anhydride has been used in the synthesis of 3,3-bis(sulfonato)-4,4-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive and photo-switchable cross-linker, D,L-7-azatryptophan, 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2,1:4,5]-2-oxazoline.

Uses

In N-acetylation of amino acids in alkaline solution; preparation of cellulose chloroacetates.

Preparation

chloroacetic anhydride Synthesis: Powdered s odium monochloroacetate(113.3g, 1.138 mol) was added slowly for a period of 15 min at room temperature (which slowly raises to 60°C) to a stirred solution of commercially available chloroaceyl chloride (127.5g, 1mol) in dry benzene (136mL) was refluxed for 9h. Salts were filtered off, the filtrate was cooled to room temperature, diluted with n-hexane and further cooled to 0°C. The solid separated was then filtered, washed with dry hexane and dried to yield chloroacetic anhydride as white crystalline compound in 60% yield (80g); mp=46-49°C [Lit. mp=46°C]. Alternatively, the benzene layer was directly subjected to high vacuum distillation.The product collected at 109-10°C at 10mm vacuum on cooling chloroacetic anhydride in lump form in 70 % yield (93g). It was observed that, the latter method gives anhydride in lump form while the former method gives in crystalline form.

Purification Methods

Crystallise the it from *benzene. [Eglinton et al. J Chem Soc 1860 1954, Beilstein 2 IV 487.]

Chloroacetic anhydride(541-88-8)Related Product Information

• Dabigatran Etexilate Mesylate
• 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
• Dabigatran etexilate
• Dabigatran
• N-(4-CYANO-PHENYL)-GLYCINE
• 4-Aminobenzamidine dihydrochloride
• 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER
• HEXYL CHLOROFORMATE
• N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride
• DICHLOROACETIC ANHYDRIDE
• TRICHLOROACETIC ANHYDRIDE
• Dichloromaleic anhydride
• Chloroacetic anhydride
• CHLORODIFLUOROACETIC ANHYDRIDE
• Chloroacetic acid
• Acetic anhydride
• Acetic acid (chloroacetic)anhydride
• CHLOROACETIC ANHYDRIDE, [2-14C]